Hydrazine hydrate (1:1) → 1H-Indazole, 5-broMo-3-(1H-pyrrol-2-yl)-

HRID 1678249Notes

Reaction equation

HRID 1678249 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([C:8]([C:10]2[NH:11][CH:12]=[CH:13][CH:14]=2)=O)[CH:7]=1.O.[NH2:17][NH2:18]>O>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:18][N:17]=[C:8]2[C:10]1[NH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22607720HCID 22607720, compound

Product 1

HCID 1357038631H-Indazole, 5-broMo-3-(1H-pyrrol-2-yl)-Yield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A slurry containing (5-bromo-2-fluoro-phenyl)-(1H-pyrrol-2-yl)-methanone (Preparation #16b, 2.40 g, 8.96 mmol) and hydrazine hydrate (35 mL) was sealed and heated by microwave iat about 150° C. for about 1 hour. The reaction was cooled to ambient temperature and diluted with water (150 mL). The product was extracted with EtOAc (150 mL), washed with 2N HCl solution (50 mL), saturated NaHCO3 solution (50 mL) and finally a saturated NaCl solution. The EtOAc layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to yield 5-bromo-3-(1H-pyrrol-2-yl)-1H-indazole (2.38 g, 99%) as an oil. RP HPLC (Table 1, Method e) Rt=2.95; m/z: (MH)+ 262/264

Workup

  1. customwas sealed
  2. temperatureThe reaction was cooled to ambient temperature
  3. extractionThe product was extracted with EtOAc (150 mL)
  4. washwashed with 2N HCl solution (50 mL), saturated NaHCO3 solution (50 mL)
  5. dry with materialThe EtOAc layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-33393f7ede55478e93e15ada9cde284c
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

Loading…